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Norelgestromin

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Also known as: Levonorgestrel oxime, Norplant 3-oxime, D-norgestrel 3-oxime, 18-methylnorethindrone oxime, 17-deacetylnorgestimate, 53016-31-2

Molecular Formula

C₂₁H₂₉NO₂

Molecular Weight

327.5 g/mol

InChI Key

ISHXLNHNDMZNMC-XUDSTZEESA-N

Norelgestromin is a drug used in contraception. Norelgestromin is the active progestin responsible for the progestational activity that occurs in women after application of ORTHO EVRA patch.

1 2D Structure

Norelgestromin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol

2.1.2 InChI

InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

2.1.3 InChI Key

ISHXLNHNDMZNMC-XUDSTZEESA-N

2.1.4 Canonical SMILES

CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=NO)CCC34

2.1.5 Isomeric SMILES

CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=NO)CC[C@H]34

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 17-deacetylnorgestimate

2. 18,19-dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, Oxime, (17alpha)-

3. Levonorgestrel Oxime

4. Levonorgestrel Oxime, (3e,17alpha)-isomer

5. Levonorgestrel Oxime, (3z,17alpha)-isomer

6. Lngo

7. Progestin Norelgestromin

2.2.2 Depositor-Supplied Synonyms

1. Levonorgestrel Oxime

2. Norplant 3-oxime

3. D-norgestrel 3-oxime

4. 18-methylnorethindrone Oxime

5. 17-deacetylnorgestimate

6. 53016-31-2

7. 17-deacylnorgestimate

8. (8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol

9. Deacetylnorgestimate

10. Norgestimate Metabolite Norelgestromin

11. Norelgestromin (17-deacetylnorgestimate)

12. Brn 4202099

13. Unii-r0tay3x631

14. Norelgestromin [usan:inn:ban]

15. Rwj 10553

16. Levonorgestrel 3-oxime

17. 17-deacetyl Norgestimate

18. 18,19-dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, Oxime, (17alpha)-

19. R0tay3x631

20. Chembl4791392

21. Dtxsid9046788

22. 13-ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one Oxime

23. Db06713

24. 18,19-dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, Oxime, (8-alpha,9-beta,10-alpha,13-alpha,14-beta)-

25. 17-deacylnorgestimate17-deacetyl Norgestimate

2.3 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₉NO₂
Molecular Weight	327.5 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	327.219829168 g/mol
Monoisotopic Mass	327.219829168 g/mol
Topological Polar Surface Area	52.8 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	642
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	1
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Norelgestromin is used for contraception and menopausal hormonal therapy. Norelgestromin may potentially be used in breast cancer treatment due to its inhibitory effect on estrone sulfatase . They convert sulfated steroid precursors to estrogen during pregnancy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Norelgestromin is used for contraception and menopausal hormonal therapy transdermally or in combination with ethinyl estradiol as a vaginal ring. Norelgestromin, in combination with ethinyl estradiol inhibits ovulation by suppressing gonadotropins.

5.2 MeSH Pharmacological Classification

Contraceptive Agents, Hormonal

Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)

5.3 ATC Code

G03AA13

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

5.4 Mechanism of Action

Norelgestromin inhibits estrone sulfatase, which converts sulfated steroid precursors to estrogen during pregnancy. Norgelgestromin/ethinylestradiol suppresses follicular development, induces changes to the endometrium, which decreases chances of implantation and thickens the cervical mucus, impeding sperm swimming into the uterus. It also has similar agonisting binding affinities as its parent compound, Norgestimate, for progesterone and estrogen receptors.

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